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Record Information |
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| Version |
1.0 |
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| Update Date |
1/22/2018 11:54:54 AM |
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Metabolite ID | PAMDB001409 |
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Identification |
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| Name: |
Sn-Glycerol-1-phosphate |
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| Description: | Sn-glycerol-1-phosphate is a glycerol phosphate. It is a key substrate in phospholipid synthesis and phosphatidylglycerol sbiosynthesis. The sn-glycerol-3-phosphate acyltransferase (plsB) of Pseudomonas aeruginosa is a key regulatory enzyme that catalyzes the first committed step in phospholipid biosynthesis. (PMID 9393688) Fosmidomycin is a hydrophilic molecule and in many bacteria its uptake is an active process involving a cAMP dependent glycerol-3-phosphate transporter (GlpT). (PMID 18489786) |
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Structure |
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| Synonyms: | - .alpha.-glycerophosphate
- .alpha.-glycerophosphorate
- .alpha.-glycerophosphoric acid
- 1,2,3-Propanetriol, 1-(dihydrogen phosphate)
- 1,2,3-Propanetriol, 1-(dihydrogen phosphoric acid)
- 1-Glycerophosphate
- 1-Glycerophosphorate
- 1-Glycerophosphoric acid
- 2,3-Dihydroxypropyl dihydrogen phosphate
- 2,3-Dihydroxypropyl dihydrogen phosphoric acid
- 2,3-Hydroxy-1-propyl dihydrogen phosphate
- 2,3-Hydroxy-1-propyl dihydrogen phosphoric acid
- 3-Glycerophosphate
- 3-Glycerophosphoric acid
- 3-Phosphoglycerol
- a-Glycerophosphate
- a-Glycerophosphorate
- a-Glycerophosphoric acid
- a-Phosphoglycerol
- alpha-Glycerophosphate
- Alpha-Glycerophosphorate
- Alpha-Glycerophosphoric acid
- Alpha-Phosphoglycerol
- BBR
- D-Glycerol 3-phosphate
- D-Glycerol 3-phosphoric acid
- Glycerol .alpha.-phosphate
- Glycerol .alpha.-phosphoric acid
- Glycerol 1-(dihydrogen phosphate)
- Glycerol 1-(dihydrogen phosphoric acid)
- Glycerol 1-phosphate
- Glycerol 1-phosphoric acid
- Glycerol 3-phosphate
- Glycerol 3-phosphoric acid
- Glycerol a-phosphate
- Glycerol a-phosphoric acid
- Glycerol alpha-phosphate
- Glycerol alpha-phosphoric acid
- Glycerol dihydrogen phosphate
- Glycerol dihydrogen phosphoric acid
- Glycerol α-phosphate
- Glycerol α-phosphoric acid
- Glycerol, 1-(dihydrogen phosphate)
- Glycerol, 1-(dihydrogen phosphate) (8CI)
- Glycerol, 1-(dihydrogen phosphoric acid)
- Glycerol, 1-(dihydrogen phosphoric acid) (8ci)
- GLYCEROL-3-PHOSPHATE
- GLYCEROL-3-phosphoric acid
- Glycerophosphate
- Glycerophosphate i
- Glycerophosphorate
- Glycerophosphorate I
- Glycerophosphoric acid
- Glycerophosphoric acid I
- L-Glycerol 1-phosphate
- L-Glycerol 1-phosphoric acid
- Sn-Glycerol 1-phosphate
- sn-Glycerol 1-phosphoric acid
- sn-Glycerol-1-phosphoric acid
- SN-glyceryl phosphate
- sn-Glyceryl phosphoric acid
- [(2S)-2,3-dihydroxypropyl] dihydrogen phosphate
- [(2S)-2,3-Dihydroxypropyl] dihydrogen phosphoric acid
- α-Glycerophosphate
- α-Glycerophosphorate
- α-Glycerophosphoric acid
- α-Phosphoglycerol
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Chemical Formula: |
C3H9O6P |
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| Average Molecular Weight: |
172.0737 |
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| Monoisotopic Molecular
Weight: |
172.013674532 |
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| InChI Key: |
AWUCVROLDVIAJX-VKHMYHEASA-N |
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| InChI: | InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m0/s1 |
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| CAS
number: |
5746-57-6 |
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| IUPAC Name: | [(2S)-2,3-dihydroxypropoxy]phosphonic acid |
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Traditional IUPAC Name: |
glycerophosphate |
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| SMILES: | [H][C@](O)(CO)COP(O)(O)=O |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as glycerophosphates. These are compounds containing a glycerol linked to a phosphate group. |
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Kingdom |
Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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Class |
Glycerophospholipids |
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| Sub Class | Glycerophosphates |
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Direct Parent |
Glycerophosphates |
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| Alternative Parents |
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| Substituents |
- Sn-glycerol-3-phosphate
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Organic phosphate
- Saccharide
- Secondary alcohol
- 1,2-diol
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
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| Molecular Framework |
Aliphatic acyclic compounds |
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| External Descriptors |
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Physical Properties |
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| State: |
Not Available |
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| Charge: | -2 |
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Melting point: |
Not Available |
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| Experimental Properties: |
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| Predicted Properties |
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Biological Properties |
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| Cellular Locations: |
Cytoplasm |
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| Reactions: | |
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Pathways: |
Not Available |
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Spectra |
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| Spectra: |
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References |
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| References: |
- Brown, A. C., Parish, T. (2008). "Dxr is essential in Mycobacterium tuberculosis and fosmidomycin resistance is due to a lack of uptake." BMC Microbiol 8:78. Pubmed: 18489786
- Heath, R. J., Goldfine, H., Rock, C. O. (1997). "A gene (plsD) from Clostridium butyricum that functionally substitutes for the sn-glycerol-3-phosphate acyltransferase gene (plsB) of Escherichia coli." J Bacteriol 179:7257-7263. Pubmed: 9393688
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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| Synthesis Reference: |
Not Available |
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| Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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| External Links: |
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